We report a ruthenium-catalyzed (2 + 2) intramolecular cycloaddition of allenes and alkenes. We have found that the use of the ruthenium complex RuH(2)Cl(2)(P(i)Pr(3))(2), which has previously gone unnoticed in catalytic applications, is crucial for the observed reactivity. The reaction proceeds under mild conditions and is fully diastereoselective, providing a practical entry to a variety of bicyclo[3.2.0]heptane skeletons featuring cyclobutane rings.
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http://dx.doi.org/10.1021/ja200784n | DOI Listing |
Tetrahedron
February 2025
Department of Chemistry, Western Washington University, Bellingham, WA 98225 (USA).
Beta-hydroxy ketones can be reduced using a sequence of ruthenium-catalyzed silyl etherification followed by tetrabutylammonium fluoride (TBAF) promoted intramolecular hydrosilylation. Switching from TBAF to tetrabutylammonium difluorotriphenylsilicate (TBAT), even without first forming the silyl ether, gave cyclic dioxasilinane products. These somewhat sensitive compounds could be isolated pure by column chromatography using florisil as the stationary phase.
View Article and Find Full Text PDFOrg Lett
April 2024
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
Phenanthridinone is a significant moiety in pharmaceutical and material science; thus, it is highly desirable to develop an efficient and robust method to construct phenanthridinone from readily available starting materials. Herein, we report a Ru-catalyzed C-H arylation of aromatic carboxylic acids with -haloanilines, followed by intramolecular dehydration to afford phenanthridinones in high yields.
View Article and Find Full Text PDFOrg Lett
May 2023
Academy of Scientific and Industrial Research (AcSIR), Ghaziabad 201002, India.
Herein, we disclose an unprecedented protocol via ruthenium-catalyzed annulation for the synthesis of 6-chromeno[4',3':4,5]imidazo[1,2-]pyridin-6-one, and functionalized 2-(3-formylimidazo[1,2-]pyridin-2-yl)phenyl acetate has been revealed by intramolecular chelation-assisted C-H activation. Additionally, a one-pot approach for creating bis(2-phenylimidazo[1,2-]pyridin-3-yl)methane (BIP) has been realized through ruthenium catalysis with the use of formic acid. This method was used in gram-scale synthesis of BIP and step-economical late-stage functionalization of a marketed drug, zolimidine, in good yield.
View Article and Find Full Text PDFAcc Chem Res
May 2023
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein Straße 4, 35043 Marburg, Germany.
ConspectusAsymmetric transition metal catalysis is an indispensable tool used both in academia and industry for forging chiral molecules in an enantioselective fashion. Its advancement relies in large part on the design and discovery of new chiral catalysts. In contrast to conventional endeavors of generating chiral transition metal catalysts from carefully tailored chiral ligands, the development of chiral transition metal catalysts containing solely achiral ligands (chiral-at-metal catalysts) has been neglected.
View Article and Find Full Text PDFMetal-catalyzed hydroarylation reactions are always powerful tools in organic synthesis since they can form C-C or C-heteroatom bonds in an atom and step economic manner. Medicinally and biologically relevant scaffolds can be easily and efficiently synthesized using this strategy. By tuning the directing groups that are present on the arenes, regioselectivity can be induced to the C-H activation.
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